Cockroach controlling compositions

ABSTRACT

Provided are compositions which include 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and at least one compound of formula (I):                    
     wherein, R 1  represents a halogen atom or a methyl group, R 2  represents a halogen atom or a methyl group and R 3  represents a hydrogen atom or a cyano group, as well as a method of controlling cockroaches.

FIELD OF THE INVENTION

The instant invention relates to compositions which may be utilized tocontrol cockroaches.

BACKGROUND OF THE INVENTION

Various compounds and compositions have been utilized to controlcockroaches, but such compounds and compositions have failed to provideeffective control of cockroaches.

U.S. Pat. No. 5,532,365 discloses1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine as a compoundwhich controls pests mainly in the agricultural arts. The pyrethroidcompounds of formula (I) below are known as compounds which controlpests in the agricultural arts and household pest controlling arts.

SUMMARY OF THE INVENTION

The instant invention provides compositions comprising1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and at least onespecified pyrethroid compound as active ingredients. The specifiedpyrethroid compound in the compositions is at least one compound offormula (I):

wherein, R₁ represents a halogen atom or methyl group, R₂ represents ahalogen atom or methyl group and R₃ represents a hydrogen atom or cyanogroup. Additionally, the instant invention provides methods ofcontrolling cockroaches comprising applying to a cockroach or to a locusof where cockroaches inhabit,1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the at leastone compound of formula (I).

DETAILED DESCRIPTION OF THE INVENTION

As mentioned above, the compositions of the instant invention utilizetherein 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and atleast one compound of formula (I):

wherein, R₁ represents a halogen atom or methyl group, R₂ represents ahalogen atom or methyl group and R₃ represents a hydrogen atom or cyanogroup.

1-Methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the at leastone compound of formula (I) which are present in the compositionstypically act as active ingredients therein. The compositions typicallycomprise such active ingredients so that the total amount of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) is from 0.005 to 50% by weight, wherein said percentageby weight is based on the total weight of the provided composition. Inthis regard, when the compositions are utilized to control cockroaches,the total amount of the active ingredients therein is typically anamount which is effective to control cockroaches. Further, thecompositions typically comprise the active ingredients so that theweight-to-weight ratio of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine to the compoundof formula (I) is from 9:1 to 1:9, preferably 3:1 to 1:3. Suchweight-to-weight ratios in the compositions can vary, but when saidcompositions are utilized to control a cockroach, said compositionsgenerally have a sufficient weight-to-weight ratio of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine to the compoundof formula (I) therein to provide a synergistic control overcockroaches.

In the compound of formula (I) of the instant invention, as R₁ or R₂ informula (I), examples of the halogen atoms include a fluorine atom, achlorine atom and a bromine atom. Said compound of formula (I) may haveR₁ and R₂ correspondingly represent identical or different substituents,such as by having R₁ and R₂ each represent methyl groups or identicalhalogen atoms.

Examples of the compound of formula (I) include 3-phenoxybenzylchrysanthemate, 3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,α-cyano-3-phenoxybenzyl chrysanthemate, α-cyano-3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,α-cyano-3-phenoxybenzyl3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate and the like.

Since the compositions can contain various active isomers of thecompound of formula (I), stereoisomers of the compound of formula (I)can be utilized in the instant invention, if so desired. When utilizing3-phenoxybenzyl chrysanthemate in the instant invention, examples of3-phenoxybenzyl chrysanthemate stereoisomers which may be utilized inthe compositions include 3-phenoxybenzyl (1RS)-cis, trans-chrysanthemate(commonly known as phenothrin), 3-phenoxybenzyl (1R)-cis,trans-chysanthemate (commonly known as d-phenothrin) and 3-phenoxybenzyl(1R)-trans-chrysanthemate. When utilizing 3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate in the instantinvention, examples of 3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate stereoisomerswhich may be utilized in the compositions include 3-phenoxybenzyl(1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(commonly known as permethrin). When utilizing α-cyano-3-phenoxybenzylchrysanthemate in the instant invention, examples ofα-cyano-3-phenoxybenzyl chrysanthemate stereoisomers which may beutilized in the compositions include (RS)-α-cyano-3-phenoxybenzyl(1R)-cis, trans-chrysanthemate (commonly known as cyphenothrin),(S)-α-cyano-3-phenoxybenzyl (1R)-cis, trans-chrysanthemate and(S)-α-cyano-3-phenoxybenzyl (1R)-trans-chrysanthemate. When utilizingα-cyano-3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate in the instantinvention, examples of α-cyano-3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate stereoisomerswhich may be utilized in the compositions include(RS)-α-cyano-3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate(commonly known as cypermethrin), (RS)-α-cyano-3-phenoxybenzyl (1R)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,(RS)-α-cyano-3-phenoxybenzyl(1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,(S)-α-cyano-3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,(S)-α-cyano-3-phenoxybenzyl (1R)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and(S)-α-cyano-3-phenoxybenzyl(1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate.

The compositions of the instant invention are typically formulated assuitable formulations of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I). Examples of such formulations of the compositionsinclude liquid formulations, dusts, wettable powders, granules, pasteformulations, microencapsulated formulations, foaming formulations,aerosol formulations, carbon dioxide formulations, tablets, cockroachbaits, smoking formulations, foggings, sheet formulations, resinformulations and the like. Examples of the liquid formulations of thecompositions include emulsifiable concentrates, oil formulations,suspensible concentrates and the like.

Such formulations of the compositions can be produced by commonly knownformulating procedures. For example, a formulation of the instantinvention can be produced by mixing together1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) and optionally adding thereto or mixing therewithformulation auxiliaries, carriers or the like. Based on the formulationtype of the compositions, said formulations may also be produced byproviding such a mixture in a suitable form, if so desired. As such, theformulations of the compositions may contain1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) without additional components, but can also contain acarrier, a formulation auxiliary or the like.

Examples of formulation auxiliaries which can be utilized in thecompositions include emulsifiers, dispersing agents such as a ligninsulfonate salt and methyl cellulose, adhesive agents such ascarboxymethyl cellulose, gum arabic, polyvinyl alcohol and polyvinylacetate, coloring agents such as iron oxide, titanium oxide, Persianblue, alizarine dye, azo dye and phthalocyanine dye and the like.Examples of the emulsifiers which can be utilized in the instantinvention include ionic emulsifiers such as an alkylsulfonate salt,alkylsulfate salt and arylsulfonate salt, nonionic emulsifiers such as apolyoxyethylene fatty acid ester, polyoxyethylenealkylaryl ether,polyoxyethylene fatty acid alcohol ether and the like.

The compositions of the instant invention generally utilize therein acarrier selected form a solid carrier, a liquid carrier and apropellant, when present.

Examples of solid carriers which can be utilized in the compositionsinclude gelatin, vaseline, methylcellulose, lanolin, lard,natural-occurring or synthetic minerals such as clay, kaolin, talc,bentonite, sericite, quartz, sulfur, activated carbon, calciumcarbonate, diatomaceous earth, pumice stone, calcite, meerschaum,dolomite, silica, alumina, vermiculite and perlite, fine granules suchas granulated sawdust, corncob, coconut shell and tobacco stems and thelike.

Examples of liquid carriers which can be utilized in the compositionsinclude liquid paraffin, aromatic or aliphatic hydrocarbons such asxylene, toluene, alkylnaphthalene, phenylxylylethane, kerosene, gasoils, hexane and cyclohexane, halogenated hydrocarbons such aschlorobenzene, dichloromethane, dichloroethane and trichloroethane,alcohols such as methanol, ethanol, isopropyl alcohol, butanol, hexanoland ethylene glycol, ethers such as diethyl ether, ethylene glycoldimethyl ether, diethylene glycol monomethyl ether, diethylene glycolmonoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran anddioxane, esters such as ethyl acetate and butyl acetate, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone,nitrites such as acetonitrile and isobutylonitrile, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, botanical oils such assoybean oil and cotton seed oil, botanical essential oils such as orangeoil, hyssop oil and lemon oil, water, sulfoxides such as dimethylsulfoxide and the like.

Examples of propellants which can be utilized in the compositionsinclude propane gas, butane gas, flon gas, liquefied petroleum gas,dimethyl ether, carbonate gas and the like. By utilizing the propellantin the compositions, the compositions may be formulated into foamingformulations, aerosol formulations, carbon dioxide formulations and thelike.

When formulating the compositions as poison baits, said poison bait canadditionally contain a bait ingredient, anti-oxidant, preservative,agent for averting unintentional child or pet ingestion of the poisonbait, cockroach attractant fragrance or the like. Examples of baitingredients which can be utilized in said poison bait include powderedcrop, botanical oil, sugar, crystallized cellulose and the like.Examples of anti-oxidants which can be utilized in said poison baitinclude dibutylhydroxytoluene, nordihydroguaiaretic acid and the like.As an example of a preservative which can be utilized in said poisonbait, there is included dehydroacetic acid and the like. As an exampleof an agent for averting unintentional child or pet ingestion of thepoison bait, there is included powdered pepper and the like. Examples ofcockroach attractant fragrances which can be utilized in said poisonbait include cheese fragrances, onion fragrances and the like.

When formulating the compositions as resin formulations, said resinformulation can additionally contain a resin material such as apolyvinyl chloride or polyurethane. Furthermore, the polyvinyl chlorideand polyurethane when utilized in the compositions may optionally have aplasticizer added thereto. Examples of plasticizers which can beutilized in the instant invention include phthalate esters such asdimethyl phthate and dioctyl phthate, adipate esters, stearate estersand the like.

Such resin formulations of the compositions can be formulated by mixingtogether 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine, thecompound of formula (I) and said resin material, and forming theresulting mixture into a desired form. For example, the resinformulations may be formulated by mixing together1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine, the compound offormula (I) and said resin material by using a standard kneading machineand then be formed into a desired form by employing a molding process.Examples of known molding processes which can be employed to formulatethe resin formulations include ejection molding, extrusion molding,press molding and the like. The resin formulations of the instantinvention can be further formed by additional molding or cutting.Examples of such resin formulations of the instant invention includeboard formulations, film formulations, tape formulations, ropeformulations, lace formulations, sheet formulations and the like.

When utilizing 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidineand the compound of formula (I) together to control cockroaches,1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) are applied to a cockroach or a locus where a control ofa cockroach is desired. As such,1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) may be utilized to control cockroaches by applying thecomposition to the cockroach or to a habitat of said cockroach.Furthermore, 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine andthe compound of formula (I) may also be utilized to control cockroachesby adding 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine andthe compound of formula (I) to products in which a control ofcockroaches is desired. In such cases,1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) may be added to synthetic resin sheets to give variouscockroach-proof products.

In utilizing 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine andthe compound of formula (I) to control cockroaches in the householdarea, 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and thecompound of formula (I) are utilized in a total amount which caneffectively control cockroaches. Such an amount of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) which can effectively control cockroaches is typically anamount of from 0.001 to 100 mg/m³. Said emulsifiable concentrates,wettable powders, flowables, microencapsulated formulations and the likeare usually diluted so that1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) can be applied at a concentration of from 0.1 to 1000ppm. In diluting such formulations of the instant invention, saidformulations may be diluted with water, if so desired. Further, said oilformulations, aerosol formulations, fogging formulations, poison baits,sheet formulations and the like usually utilize1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) together to control cockroaches without dilution.

In utilizing the compositions to control cockroaches, examples of suchcockroaches include German cockroach (Blattella germanica), smokybrowncockroach (Periplaneta fuliginosa), American cockroach (Periplanetaamericana), brown cockroach (Periplaneta brunnea), oriental cockroach(Blatta orientalis) and the like.

It should be noted that1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I) can be applied together to a cockroach or a locus wherecockroaches inhabit by employing various methods. For example, as amethod of applying1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and the compoundof formula (I), there are mentioned methods which have said activeingredients applied to a locus as a mixture that is the composition ofthe instant invention or as separately in a sequential manner. As anexample of the latter type of method, at least one of the activeingredients is applied to a locus and then the other activeingredient(s) is applied to said locus. Such latter type of the methodsinclude applying 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidineand the compound of formula (I) to a locus in a separate but essentiallysimultaneous manner, wherein the active ingredients are present inseparate compositions that are applied to a locus at an essentiallysimultaneous time or within an essentially simultaneous timeframe.

Furthermore, the compositions may also comprise additional activeingredients. Examples of such additional active ingredients which may beutilized in the compositions include organophosphorous compounds,carbamate compounds, N-phenylpyrazole compounds, synergists and thelike. Examples of organophosphorous compounds which may be utilized inthe compositions include dichlorvos, tetrachlorovinphos, fenthion,chlorpyrifos, diazinon and the like. Examples of carbamate compoundswhich may be utilized in the compositions include propoxur, carbaryl,metoxadiazone, fenobucarb and the like. Examples of synergists which maybe utilized in the compositions include PBO, S421, MGK 264, IBTA and thelike.

EXAMPLES Formulation Example 1

(Emulsifiable Concentrate)

Two and one-half (2.5) parts by weight of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine, 2.5 parts byweight of (S)-α-cyano-3-phenoxybenzyl (1R)-cis,trans-chrysanthemate, 8parts by weight of polyoxyethylenealkylaryl ether, 2 parts by weight ofsodium alkylarylsulfonate and 85 parts by weight of xylene are mixedtogether to provide an emulsifiable concentrate of the instantinvention.

Formulation Example 2

(Aerosol Formulation)

One-tenth (0.1) part by weight of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine, 0.1 part byweight of 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate, 30 parts byweight of isopropyl alcohol and 29.8 parts by weight of distilled waterare mixed together, are dissolved therein and are placed in an aerosolcontainer. A valve component is connected to the aerosol container and40 parts by weight of liquefied petroleum gas (LPG) is packed into theaerosol container, to provide a water-based aerosol formulation of theinstant invention.

Formulation Example 3

(Fogging formulation)

Five (5) parts by weight of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine, 5 parts byweight of 3-phenoxybenzyl(1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,7 parts by weight of ethyl oleate, 0.5 parts by weight of zinc oxide and2 parts by weight of α-starch are mixed together in a foaming agent toan amount of 100 parts by weight. Water is added to the mixture.Subsequently, the mixture is kneaded, is formed into granules with anextrusion machine and is allowed to dry. In a container sectioned by analuminum wall divider, 2 grams of said granules are placed into onesection thereof and 50 grams of magnesium oxide are placed into theother section thereof, to provide a fogging formulation.

Formulation Example 4

A mixture is produced by mixing together 0.1 part by weight of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and 0.1 part byweight of a composition containing 3-phenoxybenzyl(1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateand 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate at a randomweight-to-weight ratio. Subsequently, 30 parts by weight of isopropylalcohol and 29.8 parts by weight of distilled water are mixed into saidmixture, are dissolved therein and are placed in an aerosol container. Avalve component is connected onto the aerosol container and 40 parts byweight of liquefied petroleum gas (LPG) is packed into the aerosolcontainer, to provide a water-based aerosol formulation of the instantinvention.

Test Example 1

Diethylene glycol monoethyl ether solutions either containing 0.4%weight by volume (w/v) of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine or 0.4% weightby volume (w/v) of 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate wereproduced. Solutions were prepared by mixing together, respectively, thesolutions containing1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and thesolutions containing 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate atratios of 1:3, 1:1 and 3:1, as provided in Table 1. The solutions andthe prepared solution mixtures were diluted with appropriate amounts ofdistilled water. In the diluted solutions, the concentrations in weightby volume (w/v) of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine thereincorresponding to 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate thereinwere 0.1/0, 0.2/0, 0.15/0.05, 0.1/0.1, 0.05/0.15, 0/0.1 and 0/0.2, asprovided in Table 1.

Triangular column shaped wooden containers containing 5 male and 5female German cockroaches (Blattela germanica) therein were placed,respectively, upright in the central region of cubic glass boxespossessing a volume of 0.34 m³ and a side length of 70 cm, and in whichsaid triangular column shaped wooden container possesses a substantiallyequilateral triangle base, a side length of 3.5 cm and a height of 15cm. Four and one-fifth milliliters (4.2 mL) of the prepared solutionswere sprayed, respectively, into the glass boxes with a spray gun. Ten(10) minutes after spraying the compositions, the cockroaches weretransferred, respectively, to sanitary containers and were provided withwater and food. The mortality rates of the cockroaches were observed 1day thereafter. The results are shown in Table 1.

TABLE 1 Compound A*/Compound B** Cockroach mortality mixing ratioconcentration (% w/v) rate (%) 100:00  0.1/0   30.0 100:00  0.2/0   40.075:25 0.15/0.05 100.0 50:50 0.1/0.1 95.0 25:75 0.05/0.15 90.0  0:100  0/0.1 0.0  0:100   0/0.2 50.0 *Compound A represents1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine **Compound Brepresents 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate

Test Example 2

Test Example 2 was conducted similar to the procedure provided in TestExample 1, but utilized 3-phenoxybenzyl(1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylatein place of 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate. The resultsare shown in Table 2.

TABLE 2 Compound A*/Compound C** Cockroach Mortality mixing ratioConcentration (% w/v) Rate (%) 100:00  0.1/0   30.0 100:00  0.2/0   40.075:25 0.15/0.05 95.0 50:50 0.1/0.1 95.0 25:75 0.05/0.15 100.0  0:100  0/0.1 10.0  0:100   0/0.2 60.0 *Compound A represents1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine **Compound Crepresents 3-phenoxybenzyl(1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Test Example 3

Test Example 3 was conducted similar to the procedure provided in TestExample 1, but utilized (RS)-α-cyano-3-phenoxybenzyl(1R)-cis,trans-chrysanthemate in place of 3-phenoxybenzyl(1R)-cis,trans-chrysanthemate. The results are shown in Table 3.

TABLE 3 Compound A*/Compound D** Cockroach mortality mixing ratioconcentration (% w/v) rate (%) 100:00  1.0/0   30.0 100:00  0.2/0   40.075:25 0.15/0.05 100.0 50:50 0.1/0.1 100.0 25:75 0.05/0.15 85.0  0:100  0/0.1 10.0  0:100   0/0.2 35.0 *Compound A represents1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine **Compound Drepresents (RS)-α-cyano-3-phenoxybenzyl (1R)-cis, trans-chrysanthemate

Comparative Example

Diethylene glycol monoethyl ether solutions either containing 0.02%weight by volume (w/v) of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine or 0.02% weightby volume (w/v) of 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate wereproduced. A solution was then prepared by mixing together, respectively,one of the solutions containing1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and one of thesolutions containing 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate at aratio of 1:1, as provided in Table 1. The solutions and the preparedsolution mixture were diluted with appropriate amounts of distilledwater. In the diluted solutions, the concentrations in weight by volume(w/v) of 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine thereincorresponding to 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate thereinwere 0.01/0, 0.02/0, 0.01/0.01 and 0/0.01, as provided in Table 4.

In cubic glass boxes possessing a volume of 0.34m³ and a side length of70cm, 10 male and 10 female adult houseflies (Musca domestica) werereleased therein, respectively. Two and one-tenth milliliters (2.1 mL)of the prepared diluted solutions are sprayed, respectively, into theglass boxes with a spray gun. Ten minutes after spraying the preparedsolutions, the cockroaches were transferred, respectively, to sanitarycontainers and were provided with water and food. The mortality rate ofthe houseflies were observed 1 day thereafter. The results are shown inTable 4.

TABLE 4 Compound A*/Compound B** Housefly Mortality mixing ratioconcentration (% w/v) Rate (%) 100:0  0.01/0   66.7 100:0  0.02/0   76.750:50 0.01/0.01 61  0:100   0/0.01 78.3 *Compound A represents1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine **Compound Brepresents 3-phenoxybenzyl (1R)-cis,trans-chrysanthemate

The above test results from the Comparative Example evidence that acomposition containing1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and3-phenoxybenzyl (1R)-cis,trans-chrysanthemate therein does not provide asynergistic control over houseflies.

What is claimed is:
 1. A cockroach-controlling composition comprisingsynergistically effective cockroach controlling amounts of1-methyl-2-nitro-3-((3-tetrahydrofuryl)methyl)guanidine and at least onecompound of formula (I):

wherein R₁ is a halogen atom or a methyl group, R₂ is a halogen atom ora methyl group and R₃ is a hydrogen atom or a cyano group.
 2. Thecomposition according to claim 1, wherein R₁ and R₂ are identicalhalogen atoms or methyl groups and R₃ is a hydrogen atom or a cyanogroup.
 3. The composition according to claim 1, wherein the compound offormula (I) is chosen from 3-phenoxybenzyl chrysanthemate,3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,α-cyano-3-phenoxybenzyl chrysanthemate and α-cyano-3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate.
 4. Thecomposition according to claim 1, wherein a weight-to-weight ratio of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine to the compoundof formula (I) is 9:1 to 1:9.
 5. The composition according to claim 1,wherein a weight-to-weight ratio of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine to the compoundof formula (1) is 3:1 to 1:3.
 6. A method of controlling cockroaches,the method comprising: applying to a cockroach or a locus where controlof cockroaches is desired, synergistically effective cockroachcontrolling amounts of1-methyl-2-nitro-3-((3-tetrahydrofuryl)methyl)guanidine and at least onecomponent of formula (I):

wherein R₁ is a halogen atom or a methyl group, R₂ is a halogen atom ora methyl group and R₃ is a hydrogen atom or a cyano group.
 7. The methodaccording to claim 6, wherein the compound of formula (I) is is chosenfrom 3-phenoxybenzyl chrysanthemate, 3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate,α-cyano-3-phenoxybenzyl chrysanthemate and α-cyano-3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate.
 8. The methodaccording to claim 6, wherein a weight-to-weight ratio of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine to the compoundof formula (I) is 9:1 to 1:9.
 9. The method according to claim 6,wherein a weight-to-weight ratio of1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine to the compoundof formula (I) is 3:1 to 1:3.